Real Estate Investment Properties for Sale in Chester, VT

Looking for investment property in Chester, VT with high ROI ?

Explore a variety of short-term homes & houses in Chester, VT. Invest wisely with VRBO & Chester, VT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Chester, VT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
160 Depot St Chester, VT Donât miss this incredible opportunity to own a lovingly maintained turn-key Victorian h...	3 beds \| 1 baths \| 1,327 sq.ft.	$225,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 8.89% Airbnb Rental Income: $1480 Traditional Rental Income: $2517 Airbnb ROI: 1.98% Traditional ROI: 8.89%
531 Main St Chester, VT Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Ch...	3 beds \| 1 baths \| 1,608 sq.ft.	$390,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 4.81% Airbnb Rental Income: $1480 Traditional Rental Income: $2579 Airbnb ROI: 0.61% Traditional ROI: 4.81%
201 Spruce Dr Chester, VT Situated on more than five acres of rolling Vermont hillside, this three bedroom, two bath...	3 beds \| 2 baths \| 3,310 sq.ft.	$889,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 1% Airbnb Rental Income: $1535 Traditional Rental Income: $2704 Airbnb ROI: -0.95% Traditional ROI: 1%
688 Hidden Heights Rd Chester, VT Classic New England Salt Box - This charming home is nestled in a hillside neighborhood w...	3 beds \| 2 baths \| 2,205 sq.ft.	$649,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.12% Airbnb Rental Income: $1480 Traditional Rental Income: $3247 Airbnb ROI: -0.52% Traditional ROI: 3.12%
127 Trombley Rd Chester, VT Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres...	5 beds \| 1 baths \| 2,856 sq.ft.	$449,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 4.38% Airbnb Rental Income: $1743 Traditional Rental Income: $3145 Airbnb ROI: -0.1% Traditional ROI: 4.38%
514 First Ave Chester, VT Built in 1803, this home has lived many lives and still stands with purpose. Set within on...	5 beds \| 5 baths \| 3,880 sq.ft.	$529,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 10.12% Airbnb Rental Income: $2857 Traditional Rental Income: $6481 Airbnb ROI: 1.45% Traditional ROI: 10.12%
106 Contro Rd Chester, VT Sweet! An just in time for the holidays. This cabin has been lived in year round and has...	2 beds \| 2 baths \| 1,475 sq.ft.	$289,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 7.33% Airbnb Rental Income: $1103 Traditional Rental Income: $2873 Airbnb ROI: -0.54% Traditional ROI: 7.33%
41 VT Route 103 S Chester, VT Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and ...	N/A beds \| N/A baths \| 2,702 sq.ft.	$299,000	Airbnb cash on cash: 0.97% Traditional cash on cash: 4.21% Airbnb Rental Income: $1675 Traditional Rental Income: $2117 Airbnb ROI: 0.97% Traditional ROI: 4.21%
2029 N Hill Rd Chester, VT Come, enjoy the quiet charm of Andover in this inviting, private Vermont homeâperfect fo...	5 beds \| 1 baths \| 2,243 sq.ft.	$369,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 6.04% Airbnb Rental Income: $1743 Traditional Rental Income: $2951 Airbnb ROI: 1.17% Traditional ROI: 6.04%
1397 Popple Dungeon Rd Chester, VT Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind...	3 beds \| 2 baths \| 1,788 sq.ft.	$399,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.55% Airbnb Rental Income: $1480 Traditional Rental Income: $3174 Airbnb ROI: -0.14% Traditional ROI: 5.55%
3630 Vt Route 103 N Chester, VT Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely reno...	3 beds \| 3 baths \| 4,324 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.63% Airbnb Rental Income: $null Traditional Rental Income: $3436 Airbnb ROI: N/A Traditional ROI: 2.63%
35 Upper Bartonsville Rd Chester, VT Looking for a turn key Vermont retreat to call your own? This beautiful home built in 2009...	2 beds \| 2 baths \| 2,016 sq.ft.	$549,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 3.13% Airbnb Rental Income: $1103 Traditional Rental Income: $2996 Airbnb ROI: -0.99% Traditional ROI: 3.13%
794 White Rd Chester, VT 794 White Rd, Chester, VT 05359 \| Single Family Residential	2 beds \| 2 baths \| 850 sq.ft.	$549,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 0.86% Airbnb Rental Income: $1103 Traditional Rental Income: $2013 Airbnb ROI: -1.64% Traditional ROI: 0.86%
717 Horsenail Hill Rd Chester, VT 717 Horsenail Hill Rd, Chester, VT 05143 \| Single Family Residential	4 beds \| 2 baths \| 2,400 sq.ft.	$749,000	Airbnb cash on cash: -2.15% Traditional cash on cash: 1.78% Airbnb Rental Income: $958 Traditional Rental Income: $3353 Airbnb ROI: -2.15% Traditional ROI: 1.78%
000 Green Mountain Tpke Chester, VT 000 Green Mountain Tpke, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 1.35% Airbnb Rental Income: $1675 Traditional Rental Income: $1189 Airbnb ROI: 1.42% Traditional ROI: 1.35%
40 Fenton Rd Chester, VT 40 Fenton Rd, Chester, VT 05143 \| Single Family Residential	4 beds \| 2 baths \| 2,148 sq.ft.	$399,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 1.61% Airbnb Rental Income: $958 Traditional Rental Income: $1773 Airbnb ROI: -1.5% Traditional ROI: 1.61%
447 Elm St Chester, VT 447 Elm St, Chester, VT 05143 \| Single Family Residential	3 beds \| 2 baths \| 1,488 sq.ft.	$369,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 4.94% Airbnb Rental Income: $1480 Traditional Rental Income: $2799 Airbnb ROI: -0.13% Traditional ROI: 4.94%
419 Coach Rd Chester, VT	3 beds \| 1 baths \| 1,440 sq.ft.	$219,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 7.48% Airbnb Rental Income: $1480 Traditional Rental Income: $2239 Airbnb ROI: 1.72% Traditional ROI: 7.48%
00 Contro Rd Chester, VT 00 Contro Rd, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$159,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 4.36% Airbnb Rental Income: $1675 Traditional Rental Income: $1189 Airbnb ROI: 4.47% Traditional ROI: 4.36%
1175 Quarry Rd Chester, VT 1175 Quarry Rd, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$290,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 1.14% Airbnb Rental Income: $1675 Traditional Rental Income: $1189 Airbnb ROI: 1.2% Traditional ROI: 1.14%
0 Snell Rd Chester, VT 0 Snell Rd, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$89,000	Airbnb cash on cash: 9.96% Traditional cash on cash: 9.76% Airbnb Rental Income: $1675 Traditional Rental Income: $1189 Airbnb ROI: 9.96% Traditional ROI: 9.76%
00 VT Route 103 N Lot 4 Chester, VT 00 VT Route 103 N Lot 4, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$115,000	Airbnb cash on cash: 7.18% Traditional cash on cash: 7.02% Airbnb Rental Income: $1675 Traditional Rental Income: $1189 Airbnb ROI: 7.18% Traditional ROI: 7.02%
00 VT Route 103 N Lot 3 Chester, VT 00 VT Route 103 N Lot 3, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$115,000	Airbnb cash on cash: 7.18% Traditional cash on cash: 7.02% Airbnb Rental Income: $1675 Traditional Rental Income: $1189 Airbnb ROI: 7.18% Traditional ROI: 7.02%
00 Vermont Route 103 Chester, VT 00 Vermont Route 103, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| 3,000 sq.ft.	$200,000	Airbnb cash on cash: 3% Traditional cash on cash: 3.98% Airbnb Rental Income: $1675 Traditional Rental Income: $1394 Airbnb ROI: 3% Traditional ROI: 3.98%
00 Quarry Rd Chester, VT 00 Quarry Rd, Chester, VT 05143 \| Other	N/A beds \| N/A baths \| N/A	$229,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.83% Airbnb Rental Income: $1675 Traditional Rental Income: $1113 Airbnb ROI: 2.27% Traditional ROI: 1.83%

Real Estate investment in Chester, VT

There are 25 properties for sale in the city of Chester . The median list price in Chester is $324,500 and the average price per square foot is $142. In March 2026, the average monthly cash on cash return in Chester is 4.00%. The average monthly rental income in Chester is $2,505.

Chester, VT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 25 investment properties available for sale in Chester.

In 2026, the best neighborhood to buy investment property is Chester.

The ROI for Long-Term is higher than the Short-Term in Chester with average rental income of $2,505.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, VT

160 Depot St

Chester, VT

3 beds | 1 baths | 1,327 sq.ft.

$225,000

Airbnb cash on cash: 1.98%

Traditional cash on cash: 8.89%

Airbnb Rental Income: $1480

Traditional Rental Income: $2517

Airbnb ROI: 1.98%

Traditional ROI: 8.89%

531 Main St

Chester, VT

3 beds | 1 baths | 1,608 sq.ft.

$390,000

Airbnb cash on cash: 0.61%

Traditional cash on cash: 4.81%

Airbnb Rental Income: $1480

Traditional Rental Income: $2579

Airbnb ROI: 0.61%

Traditional ROI: 4.81%

201 Spruce Dr

Chester, VT

3 beds | 2 baths | 3,310 sq.ft.

$889,000

Airbnb cash on cash: -0.95%

Traditional cash on cash: 1%

Airbnb Rental Income: $1535

Traditional Rental Income: $2704

Airbnb ROI: -0.95%

Traditional ROI: 1%

688 Hidden Heights Rd

Chester, VT

3 beds | 2 baths | 2,205 sq.ft.

$649,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 3.12%

Airbnb Rental Income: $1480

Traditional Rental Income: $3247

Airbnb ROI: -0.52%

Traditional ROI: 3.12%

127 Trombley Rd

Chester, VT

5 beds | 1 baths | 2,856 sq.ft.

$449,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $1743

Traditional Rental Income: $3145

Airbnb ROI: -0.1%

Traditional ROI: 4.38%

514 First Ave

Chester, VT

5 beds | 5 baths | 3,880 sq.ft.

$529,000

Airbnb cash on cash: 1.45%

Traditional cash on cash: 10.12%

Airbnb Rental Income: $2857

Traditional Rental Income: $6481

Airbnb ROI: 1.45%

Traditional ROI: 10.12%

106 Contro Rd

Chester, VT

2 beds | 2 baths | 1,475 sq.ft.

$289,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 7.33%

Airbnb Rental Income: $1103

Traditional Rental Income: $2873

Airbnb ROI: -0.54%

Traditional ROI: 7.33%

41 VT Route 103 S

Chester, VT

N/A beds | N/A baths | 2,702 sq.ft.

$299,000

Airbnb cash on cash: 0.97%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $1675

Traditional Rental Income: $2117

Airbnb ROI: 0.97%